1-Benzoyl-2-isopropylhydrazine → HCID 71468731, compound

HRID 1401083Notes

Reaction equation

HRID 1401083 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](/[CH:11]=[CH:12]/[C:13]([OH:15])=O)=[CH:3]1.[CH:16]([NH:19][NH:20][C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:18])[CH3:17].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C.CCOC(C)=O>[CH:16]([N:19]([C:13](=[O:15])/[CH:12]=[CH:11]/[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:2]([CH3:1])[CH:3]=1)[NH:20][C:21](=[O:28])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 188691-Benzoyl-2-isopropylhydrazineHCID 81531DiisopropylethylamineHCID 5965649(E)-3-(1-methyl-1H-indol-3-yl)acrylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 71468731HCID 71468731, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To solution containing (E)-3-(1-methyl-1H-indol-3-yl)acrylic acid (50 mg, 0.24 mmol, 1.0 equivalent), N′-isopropylbenzohydrazide (66.43 mg, 0.37 mmol, 1.5 equivalent) and HATU (141.72 mg, 0.37 mmol, 1.5 equivalent) dissolved in DMF (5.0 ml), N,N-diisopropylethylamine (DIPEA)(0.06 ml, 0.37 mmol, 1.5 equivalent) was slowly drop-wise added and stirred at room temperature for 24 hr. The reaction mixture was diluted with EtOAc, washed with water and brine, dried with anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was separated through silica gel chromatography (n-hexane:EtOAc:methanol=9:3:1) and dried so that white solid form of (E)-N′-isopropyl-N′-(3-(1-methyl-1H-indol-3-yl)acryloyl)benzohydrazide was obtained.(82.62 mg, 92%).

Workup

  1. washwashed with water and brine
  2. dry with materialdried with anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated through silica gel chromatography (n-hexane:EtOAc:methanol=9:3:1)
  6. dry with materialdried so that white solid form of (E)-N′-isopropyl-N′-(3-(1-methyl-1H-indol-3-yl)acryloyl)benzohydrazide
  7. customwas obtained

Sources & evidence

ORD record
ord-4a8a5bf46f7a4669bba82167b548ffed
Source dataset
uspto-grants-2014_12
Patent number
US08906952B2

Reaction notes

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